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447447

Sigma-Aldrich

(4S,5R)-(−)-cis-4,5-Diphenyl-2-oxazolidinone

98%

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Empirical Formula (Hill Notation):
C15H13NO2
CAS Number:
23204-70-8
Molecular Weight:
239.27
MDL number:
MFCD00799526
UNSPSC Code:
12352005
PubChem Substance ID:
24868340
NACRES:
NA.22

Assay

98%

optical activity

[α]23/D −57±4°, c = 2 in chloroform (or methanol)

mp

227-232 °C (lit.)

SMILES string

O=C1N[C@H]([C@H](O1)c2ccccc2)c3ccccc3

InChI

1S/C15H13NO2/c17-15-16-13(11-7-3-1-4-8-11)14(18-15)12-9-5-2-6-10-12/h1-10,13-14H,(H,16,17)/t13-,14+/m0/s1

InChI key

LTENIVFVXMCOQI-UONOGXRCSA-N

Application

Versatile chiral auxiliary used in a variety of highly diastereoselective reactions such as Michael additions, Diels-Alder reactions, cyclopropanations, and allylations.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Davies, I.W. et al.
Tetrahedron Letters, 36, 7619-7619 (1995)
Akiba, T. et al.
Tetrahedron, 50, 3905-3905 (1994)
Arun K. Ghosh et al.
The Journal of organic chemistry, 61(18), 6175-6182 (1996-09-06)
Sinefungin (1) a nucleoside antibiotic isolated from Streptomyces has been synthesized from D-ribose. Both the C-6 and C-9 stereogenic centers were constructed by efficient asymmetric syntheses. The C-6 amine stereochemistry was set by a highly diastereoselective allylation (>99% de) of
Davies, S.G. Sanganee, H.J.
Tetrahedron Asymmetry, 6, 671-671 (1995)

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